Diisopropylethylamine → Methyl 3-(cyclopropyl(methyl)amino)-2-oxo-1,2-dihydroquinoxaline-6-carboxylate

HRID 1403503Notes

Reaction equation

HRID 1403503 reaction equation
Cl[C:2]1[C:3](=[O:16])[NH:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=2.CC[N:19]([CH:23]([CH3:25])[CH3:24])[CH:20](C)C.Cl.CNC1CC1>CS(C)=O.O>[CH:23]1([N:19]([CH3:20])[C:2]2[C:3](=[O:16])[NH:4][C:5]3[C:10]([N:11]=2)=[CH:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=3)[CH2:24][CH2:25]1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 18546974N-methylcyclopropanamine hydrochlorideHCID 68194304Methyl 3-chloro-2-oxo-1,2-dihydroquinoxaline-6-carboxylate

Product 1

HCID 70654244Methyl 3-(cyclopropyl(methyl)amino)-2-oxo-1,2-dihydroquinoxaline-6-carboxylateYield 91%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of methyl 3-chloro-2-oxo-1,2-dihydroquinoxaline-6-carboxylate (750 mg, 3.14 mmol) in DMSO (5 ml) was added DIEA (812.7 mg, 6.29 mmol), N-methylcyclopropanamine hydrochloride (450 mg, 4.18 mmol) with stirring for 3 h at 75° C. in an oil bath. The resulting solution was diluted with water (200 ml), and the product was collected by filtration to give methyl 3-[cyclopropyl(methyl)amino]-2-oxo-1,2-dihydroquinoxaline-6-carboxylate as a solid (780 mg, 91%).

Workup

  1. filtrationthe product was collected by filtration

Sources & evidence

ORD record
ord-06036d76f340475c963ef8d2a823aa5c
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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